Fragmentation of nitrone triflates to 9-membered rings

John A. Murphy; Mohan Mahesh; Gary McPheators; R. Vijaya Anand; Thomas M. McGuire; Robert Carling; Alan R. Kennedy

doi:10.1021/ol071049d

Fragmentation of nitrone triflates to 9-membered rings

John A. Murphy, Mohan Mahesh, Gary McPheators, R. Vijaya Anand, Thomas M. McGuire, Robert Carling, Alan R. Kennedy

Research output: Contribution to journal › Article › peer-review

16 Citations (Scopus)

Abstract

A new fragmentative rearrangement of nitrone derivatives to form 9-membered rings is reported. The fragmentations are triggered when nitrones are treated with triflic anhydride; a C-C bond antiperiplanar to the cleaving N-O bond is activated either by an oxygen lone pair or by an electron-rich aromatic ring. In the former case, further cyclization of the 9-membered intermediate leads to a rearranged condensed ring system, but when triggered by arenes, 9-membered ring amides are isolated.

Original language	English
Pages (from-to)	3233-3236
Number of pages	4
Journal	Organic Letters
Volume	9
Issue number	17
DOIs	https://doi.org/10.1021/ol071049d
Publication status	Published - 16 Aug 2007

Keywords

nitrone triflates
cyclization
amides

Access to Document

10.1021/ol071049d

x-ray diffractometer
Kennedy, A.
Pure And Applied Chemistry
Facility/equipment: Equipment

Cite this

@article{733546e209b34072aca45b3bf17006d1,

title = "Fragmentation of nitrone triflates to 9-membered rings",

abstract = "A new fragmentative rearrangement of nitrone derivatives to form 9-membered rings is reported. The fragmentations are triggered when nitrones are treated with triflic anhydride; a C-C bond antiperiplanar to the cleaving N-O bond is activated either by an oxygen lone pair or by an electron-rich aromatic ring. In the former case, further cyclization of the 9-membered intermediate leads to a rearranged condensed ring system, but when triggered by arenes, 9-membered ring amides are isolated.",

keywords = "nitrone triflates , cyclization , amides ",

author = "Murphy, {John A.} and Mohan Mahesh and Gary McPheators and Anand, {R. Vijaya} and McGuire, {Thomas M.} and Robert Carling and Kennedy, {Alan R.}",

year = "2007",

month = aug,

day = "16",

doi = "10.1021/ol071049d",

language = "English",

volume = "9",

pages = "3233--3236",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

number = "17",

}

TY - JOUR

T1 - Fragmentation of nitrone triflates to 9-membered rings

AU - Murphy, John A.

AU - Mahesh, Mohan

AU - McPheators, Gary

AU - Anand, R. Vijaya

AU - McGuire, Thomas M.

AU - Carling, Robert

AU - Kennedy, Alan R.

PY - 2007/8/16

Y1 - 2007/8/16

N2 - A new fragmentative rearrangement of nitrone derivatives to form 9-membered rings is reported. The fragmentations are triggered when nitrones are treated with triflic anhydride; a C-C bond antiperiplanar to the cleaving N-O bond is activated either by an oxygen lone pair or by an electron-rich aromatic ring. In the former case, further cyclization of the 9-membered intermediate leads to a rearranged condensed ring system, but when triggered by arenes, 9-membered ring amides are isolated.

AB - A new fragmentative rearrangement of nitrone derivatives to form 9-membered rings is reported. The fragmentations are triggered when nitrones are treated with triflic anhydride; a C-C bond antiperiplanar to the cleaving N-O bond is activated either by an oxygen lone pair or by an electron-rich aromatic ring. In the former case, further cyclization of the 9-membered intermediate leads to a rearranged condensed ring system, but when triggered by arenes, 9-membered ring amides are isolated.

KW - nitrone triflates

KW - cyclization

KW - amides

U2 - 10.1021/ol071049d

DO - 10.1021/ol071049d

M3 - Article

SN - 1523-7060

VL - 9

SP - 3233

EP - 3236

JO - Organic Letters

JF - Organic Letters

IS - 17

ER -

Fragmentation of nitrone triflates to 9-membered rings

Abstract

Keywords

Access to Document

Fingerprint

Equipment

x-ray diffractometer

Cite this